Chastity Thoughts

Since the start of the year, I've been working towards being in chastity whenever I'm not with my lady.  It's been a bit on and off, but since Monday, except for my morning shower and cleaning, I've been locked up nearly 100% of the time that I wasn't with her or about to be.  Day time lock up isn't that difficult.  I do find that it helps me avoid masturbating, even though I have the key readily available.  It's much more of a pre-mediated event to unlock myself before self-pleasuring.  That extra step is enough to help me abstain.

I suppose my purposes for doing are (1) to save myself for her, (2) to maintain that certain arousal buzz that goes along with wearing a device, and (3) feed my submissive urges.

Throughout the week, I've worn the device while in the hot tub, while running on my treadmill, and while working out on my home gym.  I wear it when I go out (which is rare these days), and all night.  Nights are definitely the most challenging.  The first few nights, I sort of tossed and turned, but since then I'm pretty used to it, until the morning erection comes along.  That's still a challenge.  It's uncomfortable but not painful.  Urinating while semi-erect and caged is definitely an event.  It takes a while, and requires a folded piece of toilet paper stuffed into the end of my HT device to capture the residual leakage.

I think I'll continue this for a while, and see how it affects my performance with my lady.  I'm hopeful that saving myself for her has a positive effect.  I'm mindful of some who report difficulty in obtaining erections, or even shrinkage after wearing a cage for extended periods.

Thanks for reading.

Jennifer

A New Year and New Opportunities

I suppose nearly all of us are glad to see 2020 in the rear view mirror.  I certainly am.

I am so very sorry for the losses and suffering the pandemic has caused.  For so many who lost loved ones or suffered from COVID-19 effects, my heart aches.  I am eternally grateful to all who have done their jobs, in healthcare particularly, but also in grocery stores, mail delivery, pharmacies and other lines of work that we have learned all too well are essential to the functioning of our society.

I must confess to being a lucky one.  Yes, my movements were restricted. Vacations, concerts, and other outings were forgone.  I continue to follow the medical experts' advice.  I wear a mask, wash my hands, limit social gatherings, and keep my distance when I have to venture out. I work from home. Those things are for me a mere nuisance. I have suffered no illness, no heartache, and no irreversible harm of any real sort as a result of the pandemic. I am fortunate and I know it. I have redoubled my efforts to provide what support I can (moral, financial, verbal) to people and places that have suffered.  I'd do more if I knew what that was.

But hey, this is a sex blog, so I must get on with the theme...

My lady and I started of the year with a bang.  Seriously.  We had the most amazing intimate moment this morning.  There really is nothing more that I love than bringing her pleasure.  I love her beyond measure, and I would do anything to make her happy.  She, like most of us I suppose, has had a difficult journey to the point in her life where we met. She is as madly in love with me as I am with her.  She characterized her orgasm as the most intense she'd ever had.  I am over the moon about that. BTW, we achieved that in a position that rhymes with "mighty fine" and is between 68 and 70.  It's a position I frankly never particularly enjoyed in previous relationships, but with her I find to be just fabulous.  It's  about the love, I think.  We are physically very compatible as well, so it's a comfortable arrangement with her on top controlling things.  Our love-making is whole body and mind. To be clear, performing oral sex on her is my hands-down favorite sexual act.  I'd forgo my own orgasm every time to bring her to one instead. She'll not stand for that though; she loves when I orgasm.

In the afterglow of our love-making, I revealed to her that I'd brought a few items of lingerie to perhaps enjoy, but we'd begun our festivities without them and I found neither opportunity nor need to introduce them.  I showed her what I brought, and also modelled a pair of pink panties with lace trim. She caressed my ass, and said she liked all of the items, and I am encouraged that she'll be happy to include them in some future love-making session. I'm glad we're taking it slowly, and I'm happy that our sex life is not centered on my crossdressing.  I don't want it to be. I want it to be about us, with props (clothing, vibrators, strap-ons, butt plugs, etc.) added as spices but not the main substance, and that's how it's been, and it's been awesome.

I really want to limit the times I orgasm while not with her, i.e. I want to minimize masturbating.  I feel like it is selfish. Although I can become erect easily at almost any time and provide her the PIV pleasure she loves, and also stimulate her orally to completion, she's made it clear to me, as I've stated, that she gains great satisfaction in inducing me to orgasm.  It's more difficult to do that if I've masturbated in the previous few days, and so I'd like to avoid that for her sake. Still, there are times when I've gone more than a week without masturbating, and not been able to orgasm when we make love, so there's more a play here than just my autoerotic stimulations.  Maybe a story for another day...

The challenge on the masturbatory front is that before I met her, Rosie Palm was my steady date.  I'm really good at masturbating.  I did it a lot.  I know what I like and what works at a particular moment.  Go figure. It's not easy to stop a long-time habit.  I'm up to the task, I think.  To address this challenge, I'm going to try to wear my Holy Trainer more often when I'm not around my love.  If I can keep my grubby mitts off my penis, then maybe I can keep from getting carried away. That's the premise.  I guess I'll let you know how it's working.  The HT feels nice, actually. It's comfortable, and a lot of times I forget I'm even wearing it.  Of course, it requires peeing sitting down, but I do that anyway, for several reasons, even if I'm unlocked.

So, what are the new opportunities I spoke of in the title of this message? Mine is first and foremost to find new ways to deepen my love for my lady.  Second, if it does not impede the first, to find the right level of crossdressing that fits within the love we have for each other.  I'm hopeful that she'll fully embrace my feminine side - signs are good thus far - but I'm prepared to limit what I do for my own selfish needs in order to maximize the pleasure I bring to her.  

Third, I hope that we can explore and incorporate more of my submissive nature into our relationship.  We've had a number of discussions about it, and she's learning what it means. She's not into giving pain, degradation, etc., and that's ok with me.  While I do confess that such activities can be a turn-on, I don't see it as a healthy behavior in a long-term relationship. I've recently been reading about sensual domination, and that direction may be a better path for the two of us. 

The thing that make our relationship magical is that she also wants my happiness as her top priority.  Did I mention that she's awesome?  She is. I'm confident that we will find a path that is mutually satisfying and builds us towards an ever deeper and longer lasting love.

Thanks for reading.

Jen

Lingerie is Introduced

My lady and I spent the afternoon together, drinking mimosas and being intimate.  As we lay naked in bed, warming up to the event, she told me "whatever you want to do, I'm good with it.  I just want you to be happy."  Seriously, she said that. We both knew what she meant, but we were both having trouble breaking past the barrier.

Finally, I screwed up the courage to ask if she'd like to see one of my lingerie items, not me wearing it, just seeing it.  I told her, "please, it's totally ok if you say, 'no,' I don't want to pressure you in any way.  If you're not comfortable, we won't do it, and it's not an issue."

She said that she wanted to see it, so I scampered off to my walk-in closet, and returned with a little green chemise.  I joked that the matching triangular thong would serve no purpose, and we both got a chuckle out of that. Unlike many CDs that we might read about, I'm not small of penis. She asked me to put in on, and so I did.  I fumbled at first, being so nervous.  Mind you, I've only had a few relationships in my life, but none ventured this far into my kink. Most women, in my limited survey, find this behavior abhorrent. When I finally managed to get the thing on correctly, she caressed it, and told me that I looked hot in it.  I could tell that she meant it. My erection grew at her touch and her remarks. 

What followed was simply remarkable. After playing for a bit, I asked her if she wanted to wear another of my pieces. She did.  I brought out a red one - Hey, Tis the Season, right?  She looked phenomenal in it; far better than I ever could.  Her womanly curves filled it out the way it was designed to be worn. She was radiant. We kissed, caressed and made love for a long time, and we each climaxed intensely.  Her first, of course, and then me. Both orgasms were extraordinary, by my observation and experience, respectively.

We lay in post-coital bliss, so contented, and so much more deeply in love than ever. She thanked me for confiding in her, and for trusting her to take the chance.  I thanked her for being open-minded, and for loving "all of me."  It was one of the most intense and pleasurable sessions we've ever had, and I think it was mostly because of the emotional connection - the trust and the openness - more than the articles of clothing.  

I'm so excited for the future. I don't know how far we'll go with this, but am happy for the journey. I am trying hard to introduce this whole world to her slowly, so as not to be overwhelming.  I am also trying to ensure that each step we take is one that she is comfortable with.  I'm prepared to stop at any point, and go no further, or even backtrack if need be. She is the most important element of my life.  I love her more than I ever thought possible, and I have never been happier in my life. Nothing is more important to me than her happiness, and that is my guiding light.`

Thanks for reading.

Jen

Crossdressing in the Time of Pandemic

I'm an office worker.  For nearly all of my career, that meant the daily slog to and from the office, through bad weather and traffic.  It also meant lack of direct sunlight for a couple of months on most days, because I would arrive at work before sunrise and depart after sunset.  Most of the time I've worked, I've not had direct access to the outside, and the lack of sunlight is depressing.

Since March, I've joined the countless millions who are fortunate enough to be able to work from home.  I would say my productivity has increased, because I spend more hours working, and less (i.e. none) on driving and idle chit-chat.  I also have nice, big windows in my home office, and can enjoy the outside views all day long.  

I'm also enjoying extended time crossdressing.  For the first time in my life, I'm able to spend hours upon hours in lady mode.  Most workday mornings, I shower, shave where needed, apply my make-up, bra and panties, breast forms, outer clothing, heels (love, love love heels!), and jewelry and wig.  My make-up skills are ok, not great.  My wardrobe continues to grow, and now with Winter upon us, I am wearing more sweater tops.  I have an array of skirts, and I love to wear them with stockings (the kind that require a garter).  In my 6" heels (with a 2" platform), I love walking around my house, feeling the softness of the nylons caressing my legs.  I am not passable as a woman; I never will be.  I'm too tall, and my face is too masculine.  But it's ok, it's not my goal.  I have to say though, that ladies clothes are so much more interesting and sexy.  It's definitely a turn-on.

How does all this jibe with my lady friend?  As I said in my first post, she loves all of me, and is supportive of me. However, she's not at the point where she wants to see me dressed that way, so out of great respect and love for her, I always revert to guy mode when we are together.  To be clear, she is a gorgeous lady - far more so than I would ever be, so there's no chance that I would outshine her. I love being the guy in our relationship.  Our romantic relationship is very good.  Our "parts" fit together quite nicely, thank you very much.  There's nothing I love more than bringing her the greatest pleasure, using every part of my anatomy.

So, for now, while I work from home, I enjoy the freedom to dress en femme as I please.  After a near lifetime of shame and embarrassment, this experience fills me with happiness and peace.

Thanks for reading!

Jen

A Toe in the Water

 Hello,

Thank you for taking the time to read this.  I'll keep the intro brief.  I'm a long-time crossdresser.  Either it has shaped my life or, more likely, the underlying nature of who I am emerges in many directions, and this is one facet.  I've been ashamed of this part of me for my whole life. It was a primary reason for my divorce, and the loss of a long-time lady friend.  They couldn't deal with it, and only added to my shame.

I'm in a new relationship now, with an amazing woman. We've been together for over a year. I love her more than I ever thought it was possible to love another person. I would endure all the hardships that led me down the road I'm on just so that I could find her again.

I was upfront with her about my past, and also about my crossdressing.  She has been incredible.  She told me that she loves all of me, the whole package.  It's as though she recognizes that so many of my other characteristics are intertwined with this one.  

Not to sound braggardly, but I do have some good qualities, like kindness, respect, empathy, and thoughtfulness. I'm submissive, an attentive lover, and a feminist. I find more joy in my lady's sexual pleasure than in my own. I'm a reasonably intelligent person. I love to learn, and to change and grow as I do.

I do not believe there is a god. I think religion is man-made (i.e. made by men, not women) and while it may have started out in pre-scientific civilization as a way to explain the unknown, it is now mostly used to sustain patriarchy.  I do not belive there is a heaven or a hell, other than what we make for ourselves and each other here in this finite existence.  I do not think humans are all that special among the living creatures. I believe animals have the capacity for many of the same emotions as humans; among them love, fear, happiness, sadness, anger, and grief.  All animals feel pain, not just cats and dogs. Thus, I am also vegan.

So, this is a story of my new life, the one with the love of my life, who loves all of me.  I guess that's enough for now.  

This is my private blog, and what I say here are my thoughts and mine alone.  If you're a kindred spirit, I'd like to hear from you.  If you're not, that's ok too, but let's not argue about it.

Regards,

Jennifer